Acyl derivative of morphin.



UNITED STA'ILES PATENT OFFICE.

HEINRICH I-IOERLEIN, OF VOHWINKEL, NEAR ELBEBFELD, GERIVIANY, ASSIGNOBTO FABBENFA'BRIKEN VCR-M. FRIEDR. BAYER & (30., OF ELBERFELD, GERMANY,A.

CORPORATION OF GERMANY.

\CYL DERIVATIVE 0F MORPHIN.

994,465. No Drawing. Application filed May 3, 1910.

To all whom. it may concern:

Be it known that I, HEINRICH Honnnnm, doctor of philosophy, chemist,citizen of the German Empire, residing at Vohwinkel, near Elberfeld,Germany, have invented new and useful Improvements in New AcylDerivatives of Morphin, of which the following is a specification.

My invention relates to a new therapeutic substance, formylmorphin, assuchand in the form of its salts.

The process for its production consists in treating morphin with formicacid. Monoformylmorphin is thus obtained. It is a white crystallinepowder soluble in dilute caustic soda lye and ives the characteri icblue color of morphin by the addition of -,chlorid of iron to itsneutral solution; which proves that the alcoholic hydroxyl group isesterified while the phenolic group is unoc cupied. It is more solublein alcohol and chloroform thaumorphin and soluble with difliculty inether and water the aqueous solution showing a strongly alkalinereaction against litmus. The new compound has the formula:- C H NO OCOHand melts at 220-225 C) It is produced according to the followingformula:

It IS less poisonous than the known acyl derivatives of morphin andshows the same valuable narcotic and soothing but a smaller hypnoticaction. It can be used" a mild narcoticagent as in cases of cough andbronchial catarrh and can also be used in the sha e of its salts, suchas the hydro chlorid wliich is easily soluble in water. The hydrochloridof formylmorphin is produced by suspending 1 part of formylmor-Specification of Letters Patent.

Serial No. 559,157.

Patented June 6, 1911.

(Spccimens.',

phin in 10 parts of absolute alcohol and adding while stirring thetheoretical amount of aqueous concentrated hydrochloric acid. Thereaction of the liquor must show acid reaction with congo paper. In thisway a clear solution is first obtained from whi h after a While the hdrochlorid crystallizes out. An average ose of the new product is about0.005 grams as a sedative, in larger doses it acts as a narcotic likemorphin.

In a vessel provided with a reflux condenser 10 parts by weight ofmorphin (free from water) are boiled for 56 hours together with 50 partsby weight of 100 per cent. formic acid. The excess of formic acid isdistilled off, water is added to the residue and the formyl morphin isprecipitated from the solution by the addition of sodium carbonate andis filtered off.

As a new articleof manufacture, formylmorphin, having the formula:

1 GUHHNOTOCOH being a white crystalline owder melting at 220-225 (3.,more 'solube in alcohol and chloroform than morphin and diflicultlysoluble in ether and water the aqueous solution showing a stronglyalkaline reaction against litmus, forming salts with acids which possessthe same therapeutical properties as the base itself, substantially asdescribed.

In testimony whereof I have hereunto set my hand in the presence of twosubscribing witnesses.

HEINRICH HOERLEIN. [L. 5.]

VVit-nesses:

Orro Komo, CHAS. J. WRIGHT.

Correction in Letters Patent No. 994,465.

It is hereby certified that in Letters Patent No. 994,465, granted June6, 1911, upon the application of Heinrich Hoerlein, of Vohwinkcl, nearElberfeld, Germany, for an improvement in Acy-l Derivatives of Morphin,an error appears n the printed specification requiring correction asfollows: Line 31, second line of formula, after the symbol NO the symbol0. should be inserted; and that the said Letters Patent should be readwith this correction therein that the same n'mv conform to the record ofthe case in the Patent Oifiee.

Signed and sealed this 8th day of August, A. D., 1911.

[SEAL] E. B. MOORE,

Commissioner of Patents.

